29169-64-0

Basic information

• Product Name: (R)-(-)-O-Formylmandeloyl chloride
• Synonyms: FORMYLOXYMANDELOYL CHLORIDE;D-(-)-O-FORMYL MANDELOYL CHLORIDE;D(-)ALPHA-FORMYLOXY-ALPHA-PHENYLACETYLCHLORIDE;R(-)-ALPHA-(FORMYLOXY)PHENYLACETYLCHLORIDE;(R)-alpha-(Chlorocarbonyl)benzyl formate;(-)-O-FORMYL-D-MANDELOYL CHLORIDE;(R)-(-)-O-FORMYLMANDELOYL CHLORIDE;(R)-O-FORMYL-MANDELOYL CHLORIDE
• CAS NO: 29169-64-0
• Molecular Formula: C₉H₇ClO₃
• Molecular Weight: 198.6
• EINECS: 249-478-4
• Product Categories: chiral
• Mol File: 29169-64-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 221 °C(lit.)
• Flash Point: >230 °F
• Appearance: light yellow clear liquid
• Density: 1.290 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: n20/D 1.523(lit.)
• Storage Temp.: 2-8°C
• BRN: 5404068
• CAS DataBase Reference: (R)-(-)-O-Formylmandeloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-O-Formylmandeloyl chloride(29169-64-0)
• EPA Substance Registry System: (R)-(-)-O-Formylmandeloyl chloride(29169-64-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 29169-64-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

(R)-(?)-O-Formylmandeloyl chloride can be used as a chiral resolving agent for the resolution of spirobiindane.

InChI:InChI=1/C9H7ClO3/c10-9(12)8(13-6-11)7-4-2-1-3-5-7/h1-6,8H/t8-/m1/s1

Upstream product

• 29169-63-9 (R)-formiloxy(phenyl)acetic acid 

Downstream Products

• 95107-09-8 (2'R,3S,5R,6R)-6-formyloxy(phenyl)acetylaminopenicillanic acid 
• 30034-03-8 cefamandole sodium salt 
• 57268-80-1 Cefamandole nafate 
• 1439390-01-8 C₂₆H₂₄N₆O₆S₂ 
• 52775-40-3 (6R)-7t-((Ξ)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 95190-67-3 4-nitrobenzyl (2'R,6R,7R)-3-acetoxymethyl-7-hydroxy(phenyl)acetylaminoceph-3-em-4-carboxylate 
• 95107-28-1 4-nitrobenzyl (5'R,6R,7S)-3-acetoxy-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylate 
• 95107-15-6 4-nitrobenzyl (3S,5R,5'R,6S)-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',6-penicillanate) 
• 95107-12-3 4-nitrobenzyl (2'R,3S,5R,6R)-6-hydroxy(phenyl)acetylaminopenicillanate 
• 95107-24-7 4-nitrobenzyl (5'R,6R,7S)-3-methyl-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylate 
• 95107-29-2 (5'R,6R,7S)-3-acetoxymethyl-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylic acid 
• 95107-27-0 (5'R,6R,7S)-3-methyl-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylic acid 
• 95107-16-7 (3S,5'R,5R,6S)-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',6-penicillanic acid) 
• 95107-11-2 4-nitrobenzyl (2'R,3S,5R,6R)-6-formyloxy(phenyl)acetylaminopenicillanate 

Relevant articles and documents

Preparation method D - (-) - formyl mandelic acid chloride

D - Mandelic acid is used. Dichloromethane is reacted with little excess of anhydrous formic acid under the catalysis of activated carbon, and a formylation reaction takes place with solid light as a dehydrating agent to obtain a colorless viscous D (-) formyl mandelic acid which is used directly in the next step without purification. The colorless viscous material D (-) formyl mandelic acid is added with dichloromethane, the activated carbon catalyst is added, the light solution is added dropwise, the heat insulation reaction is finished, and the methylene chloride is distilled and recovered, and the colorless and transparent liquid is D (-) formyl mandelic acid chloride. The reaction is mild and environment-friendly, the reaction conversion rate and the product purity can be effectively improved, the production cost is effectively reduced, the operation is simple and convenient, and the industrial production is facilitated.

Spirocyclic Side-chain Derivatives of Penicillin and Cephalosporin

A series of two spirocyclic oxazolidinone derivatives of penicillin and four derivatives of cephalosporin have been prepared, as well as a benzoxazine conjugate of cephalosporin, with the object of freezing the conformation of the 6(7)-amide side-chain bearing a pendant aromatic ring.The antibacterial properties of these derivatives are discussed.