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122-51-0 - Triethyl orthoformate, 98% - Ethyl orthoformate - Orthoformic acid triethyl ester - A13587 - Alfa Aesar

A13587 Triethyl orthoformate, 98%

CAS 번호
122-51-0
동의어
Ethyl orthoformate
Orthoformic acid triethyl ester

사이즈 가격 ($) 수량 재고 여부
500ml 34.50
2500ml 110.00
10000ml 366.00
장바구니에 추가 대량 견적에 추가 항목 보기

Triethyl orthoformate, 98%

MDL
MFCD00009230
EINECS
204-550-4

화학적 특성

화학식
C7H16O3
화학 식량
148.20
융점
-61°
비등점
144-146°
인화점
30°(86°F)
밀도
0.891
굴절률
1.3910
감도
Moisture Sensitive
용해도
Miscible with alcohols, acetone, ethers and chloroform. Slightly miscible with water.

용도

Triethyl orthoformate is used in Bodroux-Chichibabin aldehyde synthesis to prepare an aldehyde with one carbon higher by reacting with Grignard reagent. It is also used in the electrophilic formylation of activated aromatic species such as phenol.

참고

Moisture sensitive. Incompatible with acids and strong oxidizing agents.

참조 문헌

Acid-catalyzed reaction with an arylamine gives the N-ethoxymethylene derivative (imidic ester); see, e.g.: Org. Synth. Coll., 4, 464 (1963); reduction (NaBH4) gives the monomethyl amine: Synthesis, 55 (1974).

Due to their intrinsic dehydrating property, orthoformates are convenient reagents for acetalization of carbonyl compounds, under acid catalysis, e.g. tosic acid: J. Am. Chem. Soc., 60, 1905 (1938); J. Org. Chem., 20, 1695 (1955), or acidic ion-exchange resin: Synthesis, 348 (1974). Selective catalysis with NBS has been found to give high yields of acetals under almost neutral conditions: Synlett, 1456 (1999).

In the presence of BF3 etherate, is a source of the diethoxycarbenium ion: Synth. Commun., 19, 2307 (1989), a selective alkylating agent and a useful intermediate for the diethoxymethylenation of ketones, to give protected ß-ketoaldehydes: J. Org. Chem., 46, 2557 (1981). For a similar reaction with enamines to give the same products, see: Chem. Lett., 1307 (1982); Bull. Chem. Soc. Jpn., 57, 1876 (1984).

Orthoformates have also found use in the electrophilic formylation of activated aromatic species, e.g.: phenols (in the presence of AlCl3): Chem. Ber., 96, 308 (1963); pyrrole derivatives (with TFA): Austral. J. Chem., 25, 1979 (1972).

For further reactions of alkyl orthoformates, see Trimethyl­ orthoformate, A13760.

Yar, M.; Shahzad, S.; Siddiqi, S. A.; Mahmood, N.; Rauf, A.; Anwar, M. S.; Chaudhry, A. A.; Rehman, I. Triethyl orthoformate mediated a novel crosslinking method for the preparation of hydrogels for tissue engineering applications: characterization and in vitro cytocompatibility analysis. Mater. Sci. Eng., C 2015, 56, 154-164.

Szczepankiewicz, W.; Kuźnik, N. Synthesis of 3-arylquinazolin-4(3H)-imines from 2-amino-N'-arylbenzamidines and triethyl orthoformate. Tetrahedron Lett. 2015, 56 (10), 1198-1199.

GHS 해저드 및 주의 설명서

해저드 설명서 (EU): H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

주의 설명서: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

기타 참조

Merck
14,6884
바일슈타인
605384
위험 등급
3
포장 그룹
III
통합 관세 코드
2915.13
TSCA(독성물질규제법)"
Yes
RTECS(화학물질 독성 등록)
RM6475000

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