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N,N-ジメチルホルムアミド

N,N-ジメチルホルムアミド 化学構造式
68-12-2
CAS番号.
68-12-2
化学名:
N,N-ジメチルホルムアミド
别名:
N,N-ジメチルホルムアミド;ホルミルジメチルアミン;ジメチルホルムアミド;N,Nジメチルホルムアミド;N,N-ジメチルホルムアミド(脱水);N,N-ジメチルホルムアミド(DMF);ジメチルホルムアミド(N,N-ジメチルホルムアミド);N,N-ジメチルホルムアミド [吸光分析用];N,N‐ジメチルホルムアミド;N,N‐ジメチルホルムアミド(脱水);N,N‐ジメチルホルムアミド(脱水) ‐SUPER‐;N,N-ジメチルホルムアミド ACS REAGENT,≥99.8%;N,N-ジメチルホルムアミド DMF;N,N-ジメチルホルムアミド PURISS. P.A.,ACS REAGENT,REAG. PH. EUR.,≥99.8% (GC);N,N-ジメチルホルムアミド TRACESELECT,FOR INORGANIC TRACE ANALYSIS,≥99.99995% (TRACE METALS ANALYSIS);N,N-ジメチルホルムアミド クロマソルブ FOR PESTICIDE RESIDUE ANALYSIS;N,N-ジメチルホルムアミド クロマソルブ GC-HEADSPACE TESTED,≥99.9%;N,N-ジメチルホルムアミド クロマソルブ PLUS,FOR HPLC,≥99.9%;N,N-ジメチルホルムアミド,ANHYDROUS;N,N-ジメチルホルムアミド,B&J BRAND
英語化学名:
N,N-Dimethylformamide
英語别名:
EMF;DMF;DMFA;U-4224;nsc5356;NSC-5356;Luvistin;DMF99.8%;99.8%DMF;DMF99.9%
CBNumber:
CB2854115
化学式:
C3H7NO
分子量:
73.09
MOL File:
68-12-2.mol

N,N-ジメチルホルムアミド 物理性質

融点 :
-61 °C
比旋光度 :
0.94 º
沸点 :
153 °C(lit.)
比重(密度) :
0.948 g/mL at 20 °C
蒸気密度:
2.5 (vs air)
蒸気圧:
2.7 mm Hg ( 20 °C)
屈折率 :
n20/D 1.430(lit.)
闪点 :
136 °F
貯蔵温度 :
Store at RT.
溶解性:
water: miscible
酸解離定数(Pka):
-0.44±0.70(Predicted)
外見 :
Powder
色:
APHA: ≤15
臭い (Odor):
Faint, ammonia-like odor detectable at 100 ppm
Relative polarity:
0.386
PH:
7 (200g/l, H2O, 20℃)
臭気閾値(Odor Threshold):
1.8ppm
爆発限界(explosive limit):
2.2-16%(V)
水溶解度 :
soluble
極大吸収波長 (λmax):
λ: 270 nm Amax: 1.00
λ: 275 nm Amax: 0.30
λ: 295 nm Amax: 0.10
λ: 310 nm Amax: 0.05
λ: 340-400 nm Amax: 0.01
Sensitive :
Hygroscopic
Merck :
14,3243
BRN :
605365
暴露限界値:
NIOSH REL: TWA 10 ppm (30 mg/m3), IDLH 500 ppm; OSHA PEL: TWA 10 ppm; ACGIH TLV: TWA 10 ppm (adopted).
InChIKey:
ZMXDDKWLCZADIW-UHFFFAOYSA-N
CAS データベース:
68-12-2(CAS DataBase Reference)
NISTの化学物質情報:
Formamide, N,N-dimethyl-(68-12-2)
IARC:
2A (Vol. 47, 71, 115) 2018
EPAの化学物質情報:
N,N-Dimethylformamide (68-12-2)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  T
Rフレーズ  61-20/21-36
Sフレーズ  53-45
RIDADR  UN 2265 3/PG 3
WGK Germany  1
RTECS 番号 LQ2100000
3-10
自然発火温度 445 °C
Hazard Note  Toxic
TSCA  Yes
国連危険物分類  3
容器等級  III
HSコード  29241990
有毒物質データの 68-12-2(Hazardous Substances Data)
毒性 LD50 in mice, rats (ml/kg): 6.8, 7.6 orally; 6.2, 4.7 i.p. (Bartsch)
消防法 危険物第4類第二石油類(水溶性)
化審法 (2)-680 優先評価化学物質
安衛法 有機則 第二種有機溶剤等
PRTR法 第一種指定化学物質
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H226 引火性の液体および蒸気 引火性液体 3 警告
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H312 皮膚に接触すると有害 急性毒性、経皮 4 警告 P280,P302+P352, P312, P322, P363,P501
H318 重篤な眼の損傷 眼に対する重篤な損傷性/眼刺激 性 1 危険 P280, P305+P351+P338, P310
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H331 吸入すると有毒 急性毒性、吸入 3 危険 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H332 吸入すると有害 急性毒性、吸入 4 警告 P261, P271, P304+P340, P312
H341 遺伝性疾患のおそれの疑い 生殖細胞変異原性 2 警告 P201,P202, P281, P308+P313, P405,P501
H360 生殖能または胎児への悪影響のおそれ 生殖毒性 1A, 1B 危険
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
H372 長期にわたる、または反復暴露により臓器の障 害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P314, P501
注意書き
P202 全ての安全注意を読み理解するまで取り扱わないこ と。
P233 容器を密閉しておくこと。
P240 容器を接地すること/アースをとること。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P271 屋外または換気の良い場所でのみ使用すること。
P303+P361+P353 皮膚(または髪)に付着した場合:直ちに汚染された衣 類をすべて脱ぐこと/取り除くこと。皮膚を流水/シャワー で洗うこと。

N,N-ジメチルホルムアミド 価格 もっと(141)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01W0104-0291 N,N-ジメチルホルムアミド 質量分率99.5+%[HCON(CH3)2](GC)
N,N-Dimethylformamide 質量分率99.5+%[HCON(CH3)2](GC)
68-12-2 25mL ¥1450 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01T02SP09 N,N-ジメチルホルムアミド, スペクトロゾール®
N,N-Dimethylformamide, Spectrosol?
68-12-2 500mL ¥6400 2018-12-26 購入
東京化成工業 D0722 N,N-ジメチルホルムアミド >99.5%(GC)
N,N-Dimethylformamide >99.5%(GC)
68-12-2 25mL ¥1600 2018-12-04 購入
東京化成工業 D0722 N,N-ジメチルホルムアミド >99.5%(GC)
N,N-Dimethylformamide >99.5%(GC)
68-12-2 100mL ¥1900 2018-12-04 購入
関東化学株式会社(KANTO) 10344-00 N,N‐ジメチルホルムアミド >99.5%(GC)
N,N‐Dimethylformamide >99.5%(GC)
68-12-2 500mL ¥1700 2018-12-13 購入

N,N-ジメチルホルムアミド MSDS


Dimethyl formamide

N,N-ジメチルホルムアミド 化学特性,用途語,生産方法

外観

無色澄明の液体ハーゼン10以下

溶解性

水及びエタノールに極めて溶けやすい。

用途

液体クロマトグラフ分析用溶離液及び溶離液調製用。フェノール樹脂、ポリアミド、尿素樹脂等高分子化合物のHPLC分析。

用途

合成皮革製造溶媒,電子工業用洗浄剤,ブタジエン抽出溶媒,有機合成反応溶媒

用途

用途及び個人専用試薬等。

用途

紫外、可視及び蛍光スペクトル分析。

用途

溶媒、試薬、触媒、選択吸収剤

用途

有機合成原料、溶剤、ガス吸収剤、触媒。

用途

ペプチド固相合成の際の保護アミノ酸の溶解や洗浄用。

用途

汎用試薬、溶剤。

使用上の注意

不活性ガス封入

説明

Dimethylformamide is an organic solvent for vinyl res ins and acetylene, butadiene and acid gases. It caused contact dermatitis in a technician at an epoxy resin manufacturers, and can provoke alcohol-induced flushing in exposed subjects.

化学的特性

N,N-Dimethylformamide is a colorless or slightly yellow liquid with a boiling point of 153°C and a vapor pressure of 380 Pa at 20°C. It is freely soluble in water and soluble in alcohols, acetone and benzene. N,N-Dimethylformamide is used as solvent, catalyst and gas absorbent. React violently with concentrated sulfuric acid, fuming nitric acid and can even explode. Pure Dimethylformamide is odorless, but industrial grade or modified Dimethylformamide has a fishy smell because it contains impurities of Dimethylamine. Dimethylformamide is unstable (especially at high temperatures) in the presence of a strong base such as sodium hydroxide or a strong acid such as hydrochloric acid or sulfuric acid, and is hydrolyzed to formic acid and dimethylamine.
N,N-Dimethylformamide Structure
N,N-Dimethylformamide structure

物理的性質

Clear, colorless to light yellow, hygroscopic, mobile liquid with a faint, characteristic, ammonialike odor. An experimentally determined odor threshold concentration of 100 ppmv was reported by Leonardos et al. (1969).

使用

N,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents.
  1. Dimethylformamide is primarily used as an industrial solvent.  Dimethylformamide solutions are used toprocess polymer fibers, films, and surface coatings; to permit easy spinning of acrylic fibers; to produce wire enamels, and as a crystallization medium in the pharmaceutical industry.
  2. DMF can also be used for formylation with alkyllithium or Grignard reagents.
  3. It is used as a reagent in Bouveault aldehyde synthesis and also in Vilsmeier-Haack reaction. It acts as a catalyst in the synthesis of acyl chlorides. It is used for separating and refining crude from olefin gas. DMF along with methylene chloride acts as a remover of varnish or lacquers. It is also used in the manufacture of adhesives, fibers and films.
  4. N,N-Dimethylformamide (DMF) is a solvent with a low evaporation rate, useful for preparing solutions with a variety of hydrophobic organic compounds used in molecular biology applications.
  5. N,N-Dimethylformamide was used to solubilize MTT crystals in cell viability assays.It was also used in feruloyl esterase activity assay in molds exhibiting high activity of the enzyme.
  6. The world-wide consumption of DMF in 2001 was approximately 285, 000 metric tonnes and most of that was used as an industrial solvent.

定義

ChEBI: A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.

調製方法

Industrial production of N,N-Dimethylformamide (DMF) is via three separate processes (Eberling 1980). Dimethylamine in methanol is reacted with carbon monoxide in the presence of sodium methoxide or metal carbonyls at 110-150°C and high pressure. Alternately, methyl formate is produced from carbon monoxide and methanol under high pressure at 60-100°C in the presence of sodium methoxide. The resulting methyl formate is distilled and then reacted with dimethylamine at 80-100°C and low pressure. The third process involves reaction of carbon dioxide, hydrogen and dimethylamine in the presence of halogen-containing transition metal compounds to yield DMF.

製造方法

Two processes are used commercially to produce dimethylformamide. In the direct or one-step process, dimethylamine and carbon monoxide react at 100°C and 200 psia in the presence of a sodium methoxide catalyst to make dimethylformamide. The homogenous catalyst is separated from the crude DMF, which is then refined to the final product. In the indirect process, methyl formate is isolated, and then reacted with dimethylamine to form DMF. To obtain methyl formate, two methods may be used - dehydrogenation of methanol and esterification of formic acid.

一般的な説明

A water-white liquid with a faint fishy odor. Flash point 136°F. Slightly less dense than water. Vapors heavier than air. Toxic by inhalation or skin absorption. May irritate eyes.

空気と水の反応

Flammable. Water soluble.

反応プロフィール

N,N-Dimethylformamide may react violently with a broad range of chemicals, e.g.: alkaline metals (sodium, potassium), azides, hydrides (sodium borohydride, lithium aluminum hydride), bromine, chlorine, carbon tetrachloride, hexachlorocyclohexane, phosphorus pentaoxide, triethylaluminum, magnesium nitrate, organic nitrates. Forms explosive mixtures with lithium azide [Bretherick, 5th ed., 1995, p. 453]. Oxidation by chromium trioxide or potassium permanganate may lead to explosion [Pal B. C. et al., Chem. Eng. News, 1981, 59, p. 47].

健康ハザード

The acute toxicity of DMF is low by inhalation, ingestion, and skin contact. Contact with liquid DMF may cause eye and skin irritation. DMF is an excellent solvent for many toxic materials that are not ordinarily absorbed and can increase the hazard of these substances by skin contact. Exposure to high concentrations of DMF may lead to liver damage and other systemic effects. Dimethylformamide is listed by IARC in Group 2B ("possible human carcinogen"). It is not classified as a "select carcinogen" according to the criteria of the OSHA Laboratory Standard. No significant reproductive effects have been observed in animal tests. Repeated exposure to DMF may result in damage to the liver, kidneys, and cardiovascular system

燃焼性と爆発性

DMF is a combustible liquid (NFPA rating = 2). Vapors are heavier than air and may travel to source of ignition and flash back. DMF vapor forms explosive mixtures with air at concentrations of 2.2 to 15.2% (by volume). Carbon dioxide or dry chemical extinguishers should be used to fight DMF fires.

工業用途

World production capacity of DMF is about 225 x 103 tons per year. The main application of DMF is as solvent in industrial processes, especially for polar polymers such as Polyvinylchloride, polyacrylonitrile and polyurethanes. DMF solutions of high molecular weight polymers are processed to fibers, films, surface coatings and synthetic leathers. Since salts can be dissolved and dissociated in DMF, the solutions are used in electrolytic capacitors and certain electrolytic processes (Eberling 1980).

接触アレルゲン

This is an organic solvent for vinyl resins and acetylene, butadiene, and acid gases. It caused contact dermatitis in a technician at an epoxy resin factory and can provoke alcohol-induced flushing in exposed subjects.

Chemical Synthesis

N,N-Dimethylformamide is predominantly produced in a single-step reaction between dimethylamine and carbon monoxide under pressure at high temperatures and in the presence of basic catalysts such as sodium methoxide. The crude product contains methanol and N,N-dimethylformamide with increased purity (up to 99.9%) is obtained by multiple distillations. Alternatively, it can be produced by a two-step process in which methyl formate is prepared separately and, in a second step, reacts with dimethylamine under similar conditions as those described for the single-step reaction. No catalysts are involved in the process.

Carcinogenicity

DMF is not carcinogenic to animals except under very high inhalation exposure conditions. No increase in tumors was seen in rats that inhaled 25, 100, or 400 ppm for 6 h/day, 5 days/week for 2 years. Similarly, no tumors were produced in mice under the same conditions for 18 months. In that chronic experiment, rats and mice were exposed by inhalation (6 h/day, 5 days/week) to 0, 25, 100, or 400 ppm DMF for 18 months (mice) or 2 years (rats). Body weights of rats exposed to 100 (males only) and 400 ppm were reduced and, conversely, body weights were increased in 400 ppm mice. Serum sorbitol dehydrogenase activity was increased in rats exposed to 100 or 400 ppm. DMF-related morphological changes in rats were observed only in the liver and consisted of increased relative liver weights, centrilobular hepatocellular hypertrophy, lipofuscin/hemosiderin accumulation in Kupffer cells, and centrilobular single cell necrosis (400 ppm only). The same liver effects were seen in all groups of mice, although the response at 25 ppm was judged as minimal.

環境運命予測

Biological. Incubation of [14C]N,N-dimethylformamide (0.1–100 μg/L) in natural seawater resulted in the compound mineralizing to carbon dioxide. The rate of carbon dioxide formation was inversely proportional to the initial concentration (Ursin, 1985).
Chemical. Reacts with acids or bases forming formic acid and dimethylamine (BASF, 1999)

代謝経路

Three urinary metabolites are identified in humans and rodents, and the metabolites quantified are N- (hydroxymethyl)-N-methylformamide (HMMF), resulting in N-methylformamide (NMF) and N-acetyl-S-(N- methylcarbamoyl)cysteine (AMCC). Ten volunteers who absorb between 28 and 60 mmol/kg DMF during an 8 h exposure to DMF in air at 6 mg=m3 excrete in the urine within 72 h between 16.1 and 48.7% of the dose as HMMF, between 8.3 and 23.9% as formamide, and between 9.7 and 22.8% as AMCC. AMCC together with HMMF is also detected in the urine of workers after occupational exposure to DMF. There is a quantitative difference between the metabolic pathway of DMF to AMCC in humans and rodents.

貯蔵

DMF should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

純化方法

DMF decomposes slightly at its normal boiling point to give small amounts of dimethylamine and carbon monoxide. The decomposition is catalysed by acidic or basic materials, so that even at room temperature DMF is appreciably decomposed if allowed to stand for several hours with solid KOH, NaOH or CaH2. If these reagents are used as dehydrating agents, therefore, they should not be refluxed with the DMF. Use of CaSO4, MgSO4, silica gel or Linde type 4A molecular sieves is preferable, followed by distillation under reduced pressure. This procedure is adequate for most laboratory purposes. Larger amounts of water can be removed by azeotropic distillation with *benzene (10% v/v, previously dried over CaH2), at atmospheric pressure: water and *benzene distil below 80o. The liquid remaining in the distillation flask is further dried by adding MgSO4 (previously ignited overnight at 300-400o) to give 25g/L. After shaking for one day, a further quantity of MgSO4 is added, and the DMF is distillied at 15-20mm pressure through a 3-ft vacuum-jacketed column packed with steel helices. However, MgSO4 is an inefficient drying agent, leaving about 0.01M water in the final DMF. More efficient drying (to around 0.001-0.007M water) is achieved by standing with powdered BaO, followed by decanting before distillation, then with alumina powder (50g/L, previously heated overnight to 500-600o), and distilling from more of the alumina, or by refluxing at 120-140o for 24hours with triphenylchlorosilane (5-10g/L), then distilling at ca 5mm pressure [Thomas & Rochow J Am Chem Soc 79 1843 1957]. Free amine in DMF can be detected by the colour reaction with 1-fluoro-2,4-dinitrobenzene. It has also been purified by drying overnight over KOH pellets and then distilling from BaO through a 10 cm Vigreux column (p 11) [Jasiewicz et al. Exp Cell Res 100 213 1976]. [For efficiency of desiccants in drying dimethylformamide see Burfield & Smithers J Org Chem 43 3966 1978, and for a review on purification, tests of purity and physical properties, see Juillard Pure Appl Chem 49 885 1977.] It has been purified by distilling from K2CO3 under high vacuum and fractionated in an all-glass apparatus. The middle fraction is collected, degassed (seven or eight freeze-thaw cycles) and redistilled under as high a vacuum as possible [Mohammad & Kosower J Am Chem Soc 93 2713 1971]. [Beilstein 4 IV 171.] Rapid purification: Stir over CaH2 (5% w/v) overnight, filter, then distil at 20mmHg. Store the distilled DMF over 3A or 4A molecular sieves. For solid phase synthesis, the DMF used must be of high quality and free from amines.

不和合性

Though stable at normal temperatures and storage conditions, DMF may react violently with halogens, acyl halides, strong oxidizers, and polyhalogenated compounds in the presence of iron. Decomposition products include toxic gases and vapors such as dimethylamine and carbon monoxide. DMF will attack some forms of plastics, rubber, and coatings.

廃棄物の処理

Excess DMF and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

N,N-ジメチルホルムアミド 上流と下流の製品情報

原材料

準備製品


N,N-ジメチルホルムアミド 生産企業

Global( 574)Suppliers
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68-12-2(N,N-ジメチルホルムアミド)キーワード:


  • 68-12-2
  • N,N-Dimethylformamide Manufacturer
  • N,N-Dimethylformamde,anhydrous
  • dimethylamidkyselinymravenci(czech)
  • Dimethylforamide
  • Dimethylformamid
  • Dimetilformamide
  • Dimetylformamidu
  • dimetylformamidu(czech)
  • dlmethylformamide
  • DMF (Amide)
  • DMF (dimethylformamide)
  • dmf(amide)
  • Dwumetyloformamid
  • dwumetyloformamid(polish)
  • Dynasolve 100
  • epapesticidechemicalcode366200
  • Formamide,N,N-dimethyl-
  • HCON(CH3)2
  • n,n-dimethyl-formamid
  • N,N-Dimethylmethanamide
  • n,n-dimetilformamida
  • NCI-C60913
  • N-Formyldimethylamine
  • nsc5356
  • NSC-5356
  • DIMETHYL FORM.L WATER, S SEAL
  • N,N-dimethylformamide absolute over mol. sieve (H2O <0.01%)
  • N,N-dimethylformamide B&J brand 4 L
  • N,N-Dimethylformamide DMF
  • N,N-DIMETHYL FORMAMIDE 99.9% MIN
  • N,N-ジメチルホルムアミド
  • ホルミルジメチルアミン
  • ジメチルホルムアミド
  • N,Nジメチルホルムアミド
  • N,N-ジメチルホルムアミド(脱水)
  • N,N-ジメチルホルムアミド(DMF)
  • ジメチルホルムアミド(N,N-ジメチルホルムアミド)
  • N,N-ジメチルホルムアミド [吸光分析用]
  • N,N‐ジメチルホルムアミド
  • N,N‐ジメチルホルムアミド(脱水)
  • N,N‐ジメチルホルムアミド(脱水) ‐SUPER‐
  • N,N-ジメチルホルムアミド ACS REAGENT,≥99.8%
  • N,N-ジメチルホルムアミド DMF
  • N,N-ジメチルホルムアミド PURISS. P.A.,ACS REAGENT,REAG. PH. EUR.,≥99.8% (GC)
  • N,N-ジメチルホルムアミド TRACESELECT,FOR INORGANIC TRACE ANALYSIS,≥99.99995% (TRACE METALS ANALYSIS)
  • N,N-ジメチルホルムアミド クロマソルブ FOR PESTICIDE RESIDUE ANALYSIS
  • N,N-ジメチルホルムアミド クロマソルブ GC-HEADSPACE TESTED,≥99.9%
  • N,N-ジメチルホルムアミド クロマソルブ PLUS,FOR HPLC,≥99.9%
  • N,N-ジメチルホルムアミド,ANHYDROUS
  • N,N-ジメチルホルムアミド,B&J BRAND
  • N.N-ジメチルホルムアミド
  • N,N-ジメチルホルムアミド, スペクトロゾール®
  • N,N-ジメチルホルミアミド
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