N,N'-ジシクロヘキシルカルボジイミド 化学特性,用途語,生産方法
外観
無色～ほとんど無色透明液体
溶解性
水に難溶 (10mg/L)。エタノール, 有機溶媒に可溶。エタノールに溶け、水にほとんど溶けない。
解説
ジシクロヘキシルカルボジイミド略号DCC．N,N′-ジシクロヘキシルチオ尿素を酸化水銀(Ⅱ)で酸化すると得られる．融点34～35 ℃，沸点154～156 ℃(1.5 kPa)．きわめて有用な脱水縮合剤であり，エステル，アミド，酸無水物，ジアシルペルオキシド，ラクトンなどの合成に使用され，みずからはジシクロヘキシル尿素となる．穏やかな条件でアミドを生成するため，ペプチド合成の重要な試薬となっている．また，オキシムなどの脱水，ジメチルスルホキシドと組み合わせてアルコールの酸化(Moffatt酸化)も行うことができる．個人差があるが，皮膚につくとはげしい炎症を起こすことがある．
用途
ペプチド合成におけるカップリング反応用。
用途
脱水縮合剤,ペプチド合成原料
用途
有機合成原料。
説明
Dicydohexyl carbodiimide is used in peptide chemistry
as a coupling reagent. It is both an irritant and a
sensitizer, and caused contact dermatitis in pharmacists
and chemists.
化学的特性
N,N0
-Dicyclohexylcarbodiimide (DCC) is
a white crystalline solid. Odor is sweet and heavy.
使用
N,N'-Dicyclohexylcarbodiimide is a carbodiimide used to couple amino acids during peptide synthesis. N,N'-Dicyclohexylcarbodiimide is used as a dehydrating agent for the preparation of amides, ketones
, nitriles as well as in the inversion and esterification of secondary alcohols.
定義
ChEBI: A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.
製造方法
A stirred mixture of N,N′-dicyclohexylurea (19.7 g), phosphorus pentoxide (100 g), sand (175 g), and pyridine (700 mL) was refluxed for 2.25 h. Stirring was no longer possible after about 30 min. The mixture was filtered and the residue was extracted with pyridine (100 mL). Pyridine was removed from the combined solutions on a flash evaporator, and the residual oil was extracted with boiling petroleum ether (bp 60–80 C°) (2 × 100 mL), and then with diethyl ether (100 mL). The combined extracts were washed with iced water (3×80 mL), dried over calcium chloride, and filtered. The solvents were removed from the filtrate under reduced pressure to give 17.4 g of an oil, which on distillation yielded 13.7 g (76%) of a clear liquid; bp 143 C° (3.5 mmHg), which solidified in the receiver; mp 34–35 C°.
Another method for producing DCC from dicyclohexylurea is a two-step process using phosphoryl chloride in dichloromethane at 40 C° for 4 h under non-basic conditions followed by removal of acidic components with aq. sodium hydroxide. This method, which gives an 89% yield of DCC, has been presented in a patent application.
一般的な説明
White crystalline solid with a heavy sweet odor.
空気と水の反応
Sensitive to moisture.
反応プロフィール
Dicyclohexylcarbodiimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). Dicyclohexylcarbodiimide is incompatible with acids and oxidizing agents. Dicyclohexylcarbodiimide reacts with water.
危険性
A poison by skin contact. Moderately toxic
by ingestion and inhalation.
火災危険
Dicyclohexylcarbodiimide is probably combustible.
接触アレルゲン
Used in peptide chemistry as a coupling reagent. It is
both an irritant and a sensitizer and has caused contact
dermatitis in pharmacists and chemists.
職業ばく露
Laboratory reagent
特徴
1,3-ジシクロヘキシル尿素の除去が困難である。この問題を解決した試薬としてEDCがある。
アミノ酸との縮合でラセミ化を起こすことがあり、HOBtなどの補助剤を利用することがある。
合成方法
1,3-ジシクロヘキシル尿素からの合成
＊問題
N,N'-ジシクロヘキシルカルクロロホルムアミジニウムクロライド（DCFC）を一度単離必要があり手間がかかる。DCFCが不安定である。
輸送方法
UN2928 Toxic solids, corrosive, organic, n.o.s.,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials, 8-
Corrosive material, Technical Name Required. UN2811
Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-
Poisonous materials, Technical Name Required
純化方法
It is sampled as a liquid after melting in warm H2O. It is sensitive to air, and it is a potent skin irritant. It can be distilled in a vacuum and is best stored in a tightly stoppered flask in a freezer. It is very soluble in CH2Cl2 and pyridine where the reaction product with H2O, after condensation, is dicyclohexyl urea which is insoluble and can be filtered off. Alternatively dissolve it in CH2Cl2, add powdered anhydrous MgSO4, shake for 4hours, filter, evaporate and distil at 0.6mm pressure and oil bath temperature of 145o. [Bodansky et al. Biochemical Preparations 10, 122 1963, Schmidt & Seefelder Justus Liebigs Ann Chem 571 83 1951, Schmidt et al. Justus Liebigs Ann Chem 612 11 1958, Beilstein 12 IV 72.]
不和合性
Dust may for explosive mixture
with air. Reacts with steam and water. N,N0
-
Dicyclohexylcarbodiimide is an amine/imide: contact
with strong oxidizers may cause fire and explosions.
Incompatible with acids, strong bases, strong reducing
agents (may form flammable gasses); azo and diazo compounds (may form toxic gases); chlorinated hydrocarbons;
nitro compounds. Contact with mixture of acetic acid 1
dinitrogen trioxide may cause explosion. The combustion
of amide compounds generate nitrogen oxides (NOx).
In the presence of moisture, may attack metals and plastics.
廃棄物の処理
Whatever cannot be saved for
recovery or recycling should be managed in an appropriate
and approved waste facility. Although not a listed RCRA
hazardous waste, this material may exhibit one or more
characteristics of a hazardous waste and require appropriate
analysis to determine specific disposal requirements.
Processing, use or contamination of this product may
change the waste management options. State and local
disposal regulations may differ from federal disposal
regulations. Dispose of container and unused contents in
accordance with federal, state and local requirements
N,N'-ジシクロヘキシルカルボジイミド 上流と下流の製品情報
原材料
準備製品