Rifamycin, 3-formyl- supplier

Name
3-FORMYL RIFAMYCIN SV
EINECS 236-311-5
CAS No. 13292-22-3
Article Data6
CAS DataBase
Density 1.37 g/cm³
Solubility
Melting Point 182-184°C
Formula C₃₈H₄₇NO₁₃
Boiling Point 855.4 °C at 760 mmHg
Molecular Weight 725.79
Flash Point 471.1 °C
Transport Information
Appearance Black-Red Solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-8-carboxaldehyde,1,2-dihydro-5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-,21-acetate (7CI,8CI);3-Formylrifampicin SV;3-Formylrifamycin;3-Formylrifamycin SV;NCI 145-635;Rifaldehyde;Rifamycin AF;
PSA 218.38000
LogP 4.70460

Synthetic route

: 13292-46-1
rifampicin

: 13292-22-3
3-formylrifamycin SV

Conditions

Conditions	Yield
With hydrogenchloride; water at 55℃; for 8h; Temperature;	95%
With hydrogenchloride; water In diethyl ether at 20℃; for 96h;	89%
With ascorbic acid In hydrogenchloride at 50℃; for 12h;
With isoniazid for 24h;

: 13292-46-1
rifampicin

: 13292-22-3
3-formylrifamycin SV

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether; water at 20℃; for 96h;	88.9%

: C38H48NO16S(1-)*Na(1+)

: 13292-22-3
3-formylrifamycin SV

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water pH=7;	78.17 g

: C38H48NO16S(1-)*K(1+)

: 13292-22-3
3-formylrifamycin SV

Conditions

Conditions	Yield
With potassium hydrogencarbonate In water pH=7;	76.34g

: 41379-00-4
N1-cinnamyl-N4-amino piperazine

: 13292-22-3
3-formylrifamycin SV

: 3-(4-cinnamylpiperazinyl iminomethyl) rifamycin SV

Conditions

Conditions	Yield
With acetic acid In ethanol at 20 - 30℃; for 2h;	98%

: 123-75-1
pyrrolidine

: 13292-22-3
3-formylrifamycin SV

: 108-10-1
4-methyl-2-pentanone

: 3-[5-methyl-3-(pyrrolidine-1-ylidenium)hex-1-ene-1-yl]rifamycin SV-8-olate

Conditions

Conditions	Yield
With acetic acid In methanol at 40 - 52℃; for 0.5h;	97.9%

...Expand

: 13292-22-3
3-formylrifamycin SV

: 3973-70-4
1-amino-4-(2-hydroxyethyl)-piperazine

: 3-(((4-(2-hydroxyethyl)-1-piperazinyl)imino)methyl)rifamycin

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.25h;	97%

: 13292-22-3
3-formylrifamycin SV

: 56964-23-9
1-amino-4-propargylpiperazine

: 56964-37-5
C45H58N4O12

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.333333h;	97%
In tetrahydrofuran for 0.25h;	94%
In tetrahydrofuran at 20℃; for 0.25h; Schlenk technique; Inert atmosphere;	91%

: 123-75-1
pyrrolidine

: 110-43-0
n-pentyl methyl ketone

: 13292-22-3
3-formylrifamycin SV

: 3-[3-(pyrrolidine-1-ylidenium)oct-1-ene-1-yl]rifamycin SV-8-olate

Conditions

Conditions	Yield
With acetic acid In methanol at 45 - 50℃; for 2h;	91.5%

...Expand

: 50-00-0
formaldehyd

: 768-94-5
1-Adamantanamine

: 13292-22-3
3-formylrifamycin SV

: C49H62N2O12

Conditions

Conditions	Yield
In pyridine for 2.75h; Ambient temperature;	90%

...Expand

: 50-00-0
formaldehyd

: 75-04-7
ethylamine

: 13292-22-3
3-formylrifamycin SV

: C41H52N2O12

Conditions

Conditions	Yield
In pyridine at 66℃; for 0.33h;	90%

...Expand

: 13987-63-8
N-Methylen-1,1,3,3-tetramethylbutylamin

: 13292-22-3
3-formylrifamycin SV

A: 3-(tert-octylimino)methyl rifamycin SV

B: C47H64N2O12

Conditions

Conditions	Yield
In pyridine at 40℃; for 2.3h;	A n/a B 88%

...Expand

: 50-00-0
formaldehyd

: 108-91-8
cyclohexylamine

: 13292-22-3
3-formylrifamycin SV

: C45H58N2O12

Conditions

Conditions	Yield
In pyridine at 42℃; for 3h;	85%

...Expand

: 50-00-0
formaldehyd

: 107-45-9
tert-Octylamine

: 13292-22-3
3-formylrifamycin SV

: C47H64N2O12

Conditions

Conditions	Yield
In pyridine at 43℃; for 4.5h;	83%

...Expand

: 123-75-1
pyrrolidine

: 2142-73-6
1-(2,5-dimethylphenyl)-1-ethanone

: 13292-22-3
3-formylrifamycin SV

: 3-[3-(2,5-dimethylphenyl)-3-(pyrrolidine-1-ylidenium)prop-1-ene-1-yl]rifamycine-SV-8-olate

Conditions

Conditions	Yield
With acetic acid In methanol at 45 - 50℃; for 1.25h;	79.3%

...Expand

: 123-75-1
pyrrolidine

: 13292-22-3
3-formylrifamycin SV

: 585-74-0
3-Methylacetophenone

: 3-[3-(3-methylphenyl)-3-(pyrrolidine-1-ylidenium)prop-1-ene-1-yl]rifamycine-SV-8-olate

Conditions

Conditions	Yield
With acetic acid In methanol at 45 - 50℃; for 1h;	78.3%

...Expand

: 50-00-0
formaldehyd

: 124-68-5
2-Amino-2-methyl-1-propanol

: 13292-22-3
3-formylrifamycin SV

: C43H56N2O13

Conditions

Conditions	Yield
In pyridine at 45℃; for 3h;	78%

...Expand

: 123-75-1
pyrrolidine

: 13292-22-3
3-formylrifamycin SV

: 89-74-7
2,4-dimethylacetophenone.

: 3-[3-(2,4-dimethylphenyl)-3-(pyrrolidine-1-ylidenium)prop-1-ene-1-yl]rifamycine-SV-8-olate

Conditions

Conditions	Yield
With acetic acid In methanol at 45 - 50℃; for 1.5h;	74.9%

...Expand

: 62937-96-6
1-ethanesulfonylpiperazine

: 13292-22-3
3-formylrifamycin SV

: C44H61N3O14S

Conditions

Conditions	Yield
Stage #1: 3-formylrifamycin SV With hydrogenchloride In ethanol; dichloromethane at 20℃; Stage #2: 1-ethanesulfonylpiperazine In methanol at 40℃; for 0.5h; Stage #3: With sodium cyanoborohydride In methanol; ethanol; dichloromethane at 20℃; for 1h;	73%

: 123-75-1
pyrrolidine

: 13292-22-3
3-formylrifamycin SV

: 577-16-2, 122382-54-1
2-Methylacetophenone

: 3-[3-(2-methylphenyl)-3-(pyrrolidine-1-ylidenium)prop-1-ene-1-yl]rifamycine-SV-8-olate

Conditions

Conditions	Yield
With acetic acid In methanol at 45 - 50℃; for 0.75h;	72.7%

...Expand

: 402927-97-3
4-amino-1-methanesulfonylpiperidine

: 13292-22-3
3-formylrifamycin SV

: C44H61N3O14S

Conditions

Conditions	Yield
Stage #1: 3-formylrifamycin SV With hydrogenchloride In ethanol; dichloromethane at 20℃; Stage #2: 4-amino-1-methanesulfonylpiperidine In methanol at 40℃; for 0.5h; Stage #3: With sodium cyanoborohydride In methanol; ethanol; dichloromethane at 20℃; for 1h;	72%

: 874218-51-6
(S)-8-(3-aminomethyl-pyrrolidin-1-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid

: 13292-22-3
3-formylrifamycin SV

: (S)-3-({[1-(3-carboxy-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-8-yl)-pyrrolidin-3-ylmethyl]-amino}-methyl)-rifamycin S

Conditions

Conditions	Yield
Stage #1: (S)-8-(3-aminomethyl-pyrrolidin-1-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid; 3-formylrifamycin SV With sodium acetate In methanol; acetic acid at 20℃; for 2h; Stage #2: With sodium cyanoborohydride In methanol; acetic acid at 20℃; for 3h;	71%

: 41717-26-4
1-(2,4,6-trimethylbenzyl)-piperazine

: 13292-22-3
3-formylrifamycin SV

: C52H69N3O12

Conditions

Conditions	Yield
Stage #1: 3-formylrifamycin SV With hydrogenchloride In ethanol; dichloromethane at 20℃; Stage #2: 1-(2,4,6-trimethylbenzyl)-piperazine In methanol at 40℃; for 0.5h; Stage #3: With sodium cyanoborohydride In methanol; ethanol; dichloromethane at 20℃; for 1h;	71%

: 50-00-0
formaldehyd

: 44855-57-4, 693-16-3
rac-2-aminooctane

: 13292-22-3
3-formylrifamycin SV

: C47H64N2O12

Conditions

Conditions	Yield
In pyridine for 5h; Ambient temperature;	70%

...Expand

: 13292-22-3
3-formylrifamycin SV

: (R/S)-3-{[1-(3-carboxy-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-8-yl)-pyrrolidin-3-yl]-hydrazinomethyl}-rifamycin SV

Conditions

Conditions	Yield
Stage #1: (R/S)-1-cyclopropyl-7-fluoro-8-(3-hydrazino-pyrrolidin-1-yl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid (trifluoroacetate salt) With sodium acetate In methanol at 0℃; for 0.0833333h; Stage #2: 3-formylrifamycin SV In methanol at 0℃; for 1h;	70%

: 13292-22-3
3-formylrifamycin SV

: 107-11-9
1-amino-2-propene

: 1332223-29-6
C41H54N2O12

Conditions

Conditions	Yield
Stage #1: 3-formylrifamycin SV; 1-amino-2-propene With hydrogenchloride; water In ethanol; dichloromethane at 45℃; for 0.5h; Stage #2: With sodium cyanoborohydride In ethanol; dichloromethane at 20℃; for 0.166667h;	70%

: 50-00-0
formaldehyd

: 13292-22-3
3-formylrifamycin SV

: 75-64-9
tert-butylamine

: (12S,3E,5S,13E,15Z)-7t-acetoxy-19-tert-butyl-15,9c,11t-trihydroxy-5r-methoxy-12,4,6t,8c,10c,12t,16-heptamethyl-19,10-dihydro-18H-2-oxa-1(2,7)-furo[2',3':5,6]benzo[1,2-g]quinazolina-cycloheptadecaphane-3,13,15-triene-11,6,11,17-tetraone

Conditions

Conditions	Yield
In pyridine at 42℃; for 3h;	69%

...Expand

: 13292-22-3
3-formylrifamycin SV

: 109-55-7
1-amino-3-(dimethylamino)propane

: C43H61N3O12

Conditions

Conditions	Yield
Stage #1: 3-formylrifamycin SV; 1-amino-3-(dimethylamino)propane With hydrogenchloride; ethanol In dichloromethane at 45℃; for 0.5h; Stage #2: With sodium cyanoborohydride at 20℃;	69%

: 768-94-5
1-Adamantanamine

: 13292-22-3
3-formylrifamycin SV

: C48H64N2O12

Conditions

Conditions	Yield
Stage #1: 3-formylrifamycin SV With hydrogenchloride In ethanol; dichloromethane at 20℃; Stage #2: 1-Adamantanamine In methanol at 40℃; for 0.5h; Stage #3: With sodium cyanoborohydride In methanol; ethanol; dichloromethane at 20℃; for 1h;	69%

: 13292-22-3
3-formylrifamycin SV

: 27469-60-9
1-(4-fluorophenyl)methyl-piperazine

: C55H65F2N3O12

Conditions

Conditions	Yield
Stage #1: 3-formylrifamycin SV With hydrogenchloride In ethanol; dichloromethane at 20℃; Stage #2: 1-(4-fluorophenyl)methyl-piperazine In methanol at 40℃; for 0.5h; Stage #3: With sodium cyanoborohydride In methanol; ethanol; dichloromethane at 20℃; for 1h;	69%

: 50-00-0
formaldehyd

: 13292-22-3
3-formylrifamycin SV

: 74-89-5
methylamine

: C40H50N2O12

Conditions

Conditions	Yield
In pyridine at 42℃; for 3.5h;	68%

...Expand

Rifamycin, 3-formyl- Specification

The Rifamycin, 3-formyl-, with CAS registry number 13292-22-3, belongs to the following product categories: (1)Various Metabolites and Impurities; (2)Intermediates & Fine Chemicals; (3)Metabolites & Impurities; (4)Pharmaceuticals. This chemical is a kind of black-red solid. Its classification code is Drug / Therapeutic Agent. And the chemical formula of this chemical is C₃₈H₄₇NO₁₃. What's more, its EINECS is 236-311-5.

Physical properties of Rifamycin, 3-formyl-: (1)ACD/LogP: 2.85; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 1.96; (4)ACD/LogD (pH 7.4): 0.24; (5)#H bond acceptors: 14; (6)#H bond donors: 6; (7)#Freely Rotating Bonds: 9; (8)Polar Surface Area: 218.38 Å²; (9)Index of Refraction: 1.633; (10)Molar Refractivity: 188.15 cm³; (11)Molar Volume: 526.5 cm³; (12)Polarizability: 74.58×10^-24cm³; (13)Surface Tension: 68.8 dyne/cm; (14)Density: 1.37 g/cm³; (15)Flash Point: 508.3 °C; (16)Enthalpy of Vaporization: 139.67 kJ/mol; (17)Boiling Point: 916.9 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)OC1C(C)C(O)C(C)C(O)C(C)\C=C\C=C(\C)C(=O)Nc4c(C=O)c(O)c3c2C(=O)C(C)(O/C=C/C(OC)C1C)Oc2c(C)c(O)c3c4O
(2)InChI: InChI=1/C38H47NO13/c1-16-11-10-12-17(2)37(48)39-28-23(15-40)32(45)25-26(33(28)46)31(44)21(6)35-27(25)36(47)38(8,52-35)50-14-13-24(49-9)18(3)34(51-22(7)41)20(5)30(43)19(4)29(16)42/h10-16,18-20,24,29-30,34,42-46H,1-9H3,(H,39,48)/b11-10+,14-13+,17-12-
(3)InChIKey: BBNQHOMJRFAQBN-AEZIOYLSBJ
(4)Std. InChI: InChI=1S/C38H47NO13/c1-16-11-10-12-17(2)37(48)39-28-23(15-40)32(45)25-26(33(28)46)31(44)21(6)35-27(25)36(47)38(8,52-35)50-14-13-24(49-9)18(3)34(51-22(7)41)20(5)30(43)19(4)29(16)42/h10-16,18-20,24,29-30,34,42-46H,1-9H3,(H,39,48)/b11-10+,14-13+,17-12-
(5)Std. InChIKey: BBNQHOMJRFAQBN-AEZIOYLSSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	416mg/kg (416mg/kg)	United States Patent Document. Vol. #4002754,
mouse	LD50	intravenous	299mg/kg (299mg/kg)	"Structure-Activity Relationship among the Semisynthetic Antibiotics," Perlman, D., ed., New York, Academic Press, 1977Vol. -, Pg. 531, 1977.
mouse	LD50	oral	907mg/kg (907mg/kg)	United States Patent Document. Vol. #4002754,

Product Name

3-FORMYL RIFAMYCIN SV

Synthetic route

Rifamycin, 3-formyl- Specification

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