36615

Sigma-Aldrich

Dicyanocobyrinic acid heptamethyl ester

≥95.0%

Synonym(s):
Heptamethyl dicyano cobyrinate
Empirical Formula (Hill Notation):
C54H73CoN6O14
CAS Number:
Molecular Weight:
1089.12
Beilstein/REAXYS Number:
1207601
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

≥95.0%

mp

124-125 °C (dec.)

storage temp.

2-8°C

SMILES string

[H][C@]12[C@H](CC(=O)OC)[C@@](C)(CCC(=O)OC)C(N1[Co](C#N)C#N)=C(C)C3=NC(=CC4=NC(=C(C)C5=N[C@]2(C)[C@@](C)(CC(=O)OC)[C@@H]5CCC(=O)OC)[C@@](C)(CC(=O)OC)[C@@H]4CCC(=O)OC)C(C)(C)[C@@H]3CCC(=O)OC

InChI

1S/C52H73N4O14.2CN.Co/c1-28-43-31(17-20-37(58)65-10)48(3,4)35(54-43)25-34-30(16-19-36(57)64-9)50(6,26-41(62)69-14)46(53-34)29(2)44-32(18-21-38(59)66-11)51(7,27-42(63)70-15)52(8,56-44)47-33(24-40(61)68-13)49(5,45(28)55-47)23-22-39(60)67-12;2*1-2;/h25,30-33,47H,16-24,26-27H2,1-15H3;;;/q-1;;;+1/t30-,31-,32-,33+,47-,49-,50+,51+,52+;;;/m1.../s1

InChI key

CPBDBBXBECBXRW-NTQATXMTSA-N

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General description

Preparation of chloro derivatives of dicyanocobyrinic acid heptamethyl ester (′cobester′) is reported.

Application

Dicyanocobyrinic acid heptamethyl ester may be used in the preparation of (5R,6R)-Coa,Coβ-dicyano-5,6-dihydro-5-hydroxy-heptamethylcob(III)yrinate-c,6-lactone, a derivative of cobyrinic acid heptamethyl ester.

Packaging

500 mg in glass bottle

Other Notes

Stable derivative of cobyrinic acid; used e.g. as catalyst for carbon-skeleton rearrangements ; Partial ester hydrolysis and prepn. of derivatives

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Y. Murakami et al.
Chemistry Letters (Jpn), 469-469 (1988)
H H Inhoffen et al.
Philosophical transactions of the Royal Society of London. Series B, Biological sciences, 273(924), 327-333 (1976-02-05)
Preparations of C10 acetate, trifluoroacetate, and chloro derivatives of dicyanocobyrinic acid heptamethyl ester ('cobester') are described. The nature and properties of intermediates in the synthesis of the 10-chloro derivative are discussed, and the electronic absorption spectra of the products are...
B. Gruning et al.
Helvetica Chimica Acta, 68, 1771-1771 (1985)
Susan M Chemaly et al.
Inorganic chemistry, 50(18), 8700-8718 (2011-08-20)
A stable yellow derivative of cobyrinic acid heptamethyl ester, (5R,6R)-Coα,Coβ-dicyano-5,6-dihydro-5-hydroxy-heptamethylcob(III)yrinate-c,6-lactone (DCSYCbs), was prepared from dicyanocobyrinic acid heptamethyl ester (DCCbs). The C5 carbon is oxidized and the c side chain cyclized to form a lactone at C6; the 13 atom, 14...
Y. Murakami et al.
Chemistry Letters (Jpn), 477-477 (1985)

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