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Squaric acid

Squaric acid 구조식 이미지
카스 번호:
2892-51-5
상품명:
Squaric acid
동의어(영문):
Squaric;2-dione;NSC 624671;squaricaci;SQUARC ACID;SQUARIC ACID;QUADRATIC ACID;obutene-1,2-dione;TIMTEC-BB SBB007891;3,4-Dihydroxy-3-cycL
CBNumber:
CB6263069
분자식:
C4H2O4
포뮬러 무게:
114.06
MOL 파일:
2892-51-5.mol

Squaric acid 속성

녹는점
>300 °C(lit.)
끓는 점
250.96°C
밀도
1.82 g/cm3
굴절률
1.5800 (estimate)
인화점
190 °C
저장 조건
Inert atmosphere,Room Temperature
용해도
20g/l
산도 계수 (pKa)
1.5??(at 25℃)
물리적 상태
Crystalline Powder
색상
White to beige
수소이온지수(pH)
1 (1g/l, H2O, 20℃)
수용성
20 g/L (30 ºC)
Merck
14,8769
BRN
774275
InChIKey
PWEBUXCTKOWPCW-UHFFFAOYSA-N
CAS 데이터베이스
2892-51-5(CAS DataBase Reference)
NIST
3-Cyclobutene-1,2-dione, 3,4-dihydroxy-(2892-51-5)
EPA
3-Cyclobutene-1,2-dione, 3,4-dihydroxy- (2892-51-5)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 36/37/38-43
안전지침서 26-36-37/39
유엔번호(UN No.) 3261
WGK 독일 3
RTECS 번호 GU1800000
위험 참고 사항 Irritant
TSCA Yes
위험 등급 8
포장분류 II
HS 번호 29144090
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.

Squaric acid MSDS


3,4-Dihydroxy-3-cyclobutene-1,2-dione

Squaric acid C화학적 특성, 용도, 생산

화학적 성질

Squaric acid (3,4-dihydroxycyclobut-3-ene-1,2-dione), also known as quadratic acid, has the fascinating structure, and is a vinylogous carboxylic acid. The parent compound is a white,crystalline powder which melts at~300℃. It is highly acidic (pKa 1.5 for the first proton and 3.4 for the second) due to resonance stabilization of the anion and exhibits IR resonances indicative of strong hydrogen bonding [2326cm-1 (OH),1818 cm-1 (C=O), and 1639cm-1 (C=C)].The UV absorption spectrum suggests that the acid is essentially completely ionized. Squaric acid is freely soluble in water but has poor solubility in many organic solvents.Solutions give an intense purple color with iron(III) chloride, and are also known to decolorize bromine water, cerium(IV) nitrate, and permanganate solutions.As the carbonyl groups are similar to those of carboxylic acids rather than those of ketones, squaric acid does not react in the phenylhydrazine test.The squarate dianion is thought to be completely symmetrical (unlike squaric acid itself), with all C-C and C-O bond lengths being, respectively, identical, as the negative charges are equally distributed between allthe oxygen atoms.The IR spectrum of dipotassium squarate (dipotassium 3,4-dioxocy-clobut-1-ene-1,2-diolate) differs greatly from that of squaric acid, with the loss of the car-bonyl (C=O) and alkene(C=C) absorptions seen in the protonated form, and supportsthe proposed symmetrical structure.

용도

Squaric acid used as intermediate for squaraine dyes and heterocycles. Squaric acid is an immunotherapy used to treat common warts. This treatment is non-toxic, and easy to use. The treatment activated your immune system to combat the warts and therefore it may cause an allergic reaction , similar to poison oak. This reaction can be managed with a topical cortisone cream. Blistering and lightening of the skin may occur, but rarely.
Squaric acid derivatives – synthetic targets for ring expansion reactions

정의

ChEBI: A carbon oxoacid that consists of 1,2-diketocyclobut-3-ene bearing two enolic hydroxy substituents at positions 3 and 4.

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 1533, 1966 DOI: 10.1021/ja00959a040
Tetrahedron Letters, 18, p. 4437, 1977

Biotechnological Applications

squaric acid is widely used in bioorganic and medicinal chemistry. It is an inhibitor of glyoxylase, semiqauric acid, pyruvate dehrogenase, and transketolase. It is used as a replacement for phosphate in a peptide-based ligand for an SH2 domain. Its derivatives are high-affinity ligands for excitatory amino acid receptors. These derivatives are also used as dyes for fluorescence detection of small biological molecules.
squaric acid can be used:
In fluorescence detection in immunoassays, hybridization assays, enzymatic reactions, and other analytical procedures.
To form diffraction quality crystals.
To synthesize a squarate dianion, which is used as a building block to create uncharged polymeric networks. These ordered structures are used in catalysis, nonlinear optics, electrical conductivity, molecular recognition, and molecular sieves.

Purification Methods

Purify squaric acid by recrystallisation from H2O — this is quite simple because the acid is ~ 7% soluble in boiling H2O and only 2% at room temperature. It is not soluble in Me2CO or Et2O; hence it can be rinsed with these solvents and dried in air or a vacuum. It is not hygroscopic and gives an intense purple colour with FeCl3. It has IR max at 1820 (C=O) and 1640 (C=C) cm-1, and UV max at 269.5nm ( 37K M-1cm -1). [Cohn et al. J Am Chem Soc 81 3480 1959, Park et al. J Am Chem Soc 84 2919 1962] See also pKa values of 0.59 ±0.09 and 3.48 ±0.023 [Scwartz & Howard J Phys Chem 74 4374 1970]. [Schmidt & Reid Synthesis 869 1978, Beilstein 8 IV 2701.]

Squaric acid 준비 용품 및 원자재

원자재

준비 용품


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