International Union of Pure and Applied Chemistry

Division VIII Chemical Nomenclature and Structure Representation Division

Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013.

Prepared for publication by Henri A. Favre and Warren H. Powell, Royal Society of Chemistry, ISBN 978-0-85404-182-4

Changes to the web Blue Book made since second version was made public on 18 December 2023.

P-13.2.2.1, example 2. [corrected 9 October 2024]
For C6H5 -P(O)(OH)2
read C6H5-P(O)(OH)2
for C6H5 -P(≡N)-OH
read C6H5-P(≡N)-OH

P-14.4 (b) lines 2/3. [corrected 28 May 2024]
For ....accommodate a substituent suffix in accordance with structural feature (d)
read ....accommodate a substituent suffix in accordance with structural feature (c)

P-16.2.4.1 (b) example 2. [corrected 9 October 2024]
For N1-(2-aminoethyl)-N1,N2,N2 -trimethylethane-1,2-diamine
read N1-(2-aminoethyl)-N1,N2,N2-trimethylethane-1,2-diamine

P-16.7.1 (a), line 2.[corrected 30 March 2024]
For ...when followed by a suffix or 'en' ending beginning with 'a', 'e'....
read ...when followed by a suffix or ending beginning with 'a', 'e'....

P-22.2.4, example 4. [corrected 9 October 2024]
For 2H-1,4,8,11-oxatriazacyclotetradecine
1-oxa-4,8,11-triazacyclotetradeca-3,5,7,9,11,13- hexaene (PIN)
read 2H-1,4,8,11-oxatriazacyclotetradecine
1-oxa-4,8,11-triazacyclotetradeca-3,5,7,9,11,13-hexaene (PIN)

P-31.1.1.1, after text. [corrected 4 September 2024]
Add If the stereochemistry of a double bond is indicated in a structure it should be specified by E or Z with the appropriate locant. This includes double bonds in rings of eight or more members (see P-91.2.2).

P-31.1.3.1, example 4. [corrected 4 September 2024]
For cyclododeca-1,5-diene (PIN)
read (1Z,5E)-cyclododeca-1,5-diene (PIN)

P-31.1.3.1, example 5. [corrected 4 September 2024]
Replace the structure with:
   
for cyclopentadec-1-en-4-yne (PIN)
read (1Z)-cyclopentadec-1-en-4-yne (PIN)

P-31.1.3.2, example 1. [corrected 4 September 2024]
For1,4,7,10-tetraoxacyclododec-2-ene (PIN)
read (2Z)-1,4,7,10-tetraoxacyclododec-2-ene (PIN)

P-31.1.3.2, example 2. [corrected 4 September 2024]
For 1-oxa-4-azacyclododec-3-ene (PIN)
read (3E)-1-oxa-4-azacyclododec-3-ene (PIN)

P-31.1.3.2, example 3. [corrected 4 September 2024]
For 1,11-disilacycloicosa-5,7-dien-3-yne (PIN)
read (5Z,7E)-1,11-disilacycloicosa-5,7-dien-3-yne (PIN)

P-31.1.3.2, example 4. [corrected 4 September 2024]
For 1,10-disilacycloicosa-12,14,16-trien-18-yne (PIN)
read (12Z,14E,16Z)-1,10-disilacycloicosa-12,14,16-trien-18-yne (PIN)

P-31.1.4.3. [corrected 4 September 2024]
The order of the three criteria changed to make minimum number of compound locants first.

P-31.1.4.3 (2) formerly (1), example. [corrected 4 September 2024]
For bicyclo[14.3.1]icosa-11,13,18-trien-2-yne (PIN)
read (11E,13E)-bicyclo[14.3.1]icosa-11,13,18-trien-2-yne (PIN)

P-31.1.4.3 (3) formerly (2), example. [corrected 4 September 2024]
For bicyclo[11.3.1]heptadeca-2-en-11-yne (PIN)
read (2Z)-bicyclo[11.3.1]heptadeca-2-en-11-yne (PIN)

P-31.1.4.3 (1) formerly (3), example. [corrected 4 September 2024]
For bicyclo[8.3.1]tetradeca-4,6,10-trien-2-yne (PIN)
read (4Z,6E)-bicyclo[8.3.1]tetradeca-4,6,10-trien-2-yne (PIN)

P-31.1.5.1.2 (1), example. [corrected 4 September 2024]
For spiro[4.10]pentadec-10-en-8-yne (PIN)
read (10Z)-spiro[4.10]pentadec-10-en-8-yne (PIN)

P-31.1.5.1.2 (2), example. [corrected 4 September 2024]
For spiro[4.10]pentadec-6-en-14-yne (PIN)
read (6E)-spiro[4.10]pentadec-6-en-14-yne (PIN)

P-31.1.6.1, before examples. [corrected 4 September 2024]
Add If there is a choice the criteria of P-31.1.4.3 are applied.

P-31.1.6.1, example 1. [corrected 4 September 2024]
Replace the structure with:
   
For 1(1,3)-benzena-9(1,3)-cyclohexanacyclohexadecaphane-91(96),94-diene (PIN)
read not 1(1,3)-benzena-9(1,3)-cyclohexanacyclohexadecaphane-91(96),94-diene
add 1(1,3)-benzena-9(1,3)-cyclohexanacyclohexadecaphane-93,95-diene (PIN)

P-31.1.6.2, example 1. [corrected 4 September 2024]
For 1,7(1,3)dibenzenacyclotridecaphan-4-en-2-yne (PIN)
read (4Z)-1,7(1,3)dibenzenacyclotridecaphan-4-en-2-yne (PIN)

P-31.1.6.2, example 2. [corrected 4 September 2024]
For 1,7(1,3)dibenzenacyclotridecaphan-2-en-5-yne (PIN)
read (2E)-1,7(1,3)dibenzenacyclotridecaphan-2-en-5-yne (PIN)

P-31.1.7.2, example 3. [corrected 9 October 2024]
For [11,21:24,31-tercyclohexane]-11(21),22,32- triene (PIN)
read [11,21:24,31-tercyclohexane]-11(21),22,32-triene (PIN)

P-31.2.4.3, example left. [corrected 4 September 2024]
For 2,3,4,5-tetrahydroazocine (PIN)
read (6Z,8Z)-2,3,4,5-tetrahydroazocine (PIN)

P-44.4.1.2 (1), example left. [corrected 4 September 2024]
For cycloicosene (PIN)
read (E)-cycloicosene (PIN)

P-44.4.1.2 (2), example left. [corrected 4 September 2024]
For cycloicosa-1,8-diene (PIN)
read (1E,8E)-cycloicosa-1,8-diene (PIN)

P-44.4.1.2 (2), example right. [corrected 4 September 2024]
For cycloicos-1-en-3-yne (PIN)
read (1E)-cycloicos-1-en-3-yne (PIN)

P-44.4.1.10.1 (1), example left. [corrected 4 September 2024]
For cyclocosa-1,3-dien-5-yne (PIN)
read (1Z,3E)-cyclocosa-1,3-dien-5-yne (PIN)

P-44.4.1.10.1 (1), example right. [corrected 4 September 2024]
For cyclocosa-1,7-dien-3-yne (PIN)
read (1E,7Z)-cyclocosa-1,7-dien-3-yne (PIN)

P-44.4.1.10.1 (2), example left. [corrected 4 September 2024]
For cyclocosa-1,3-dien-5-yne (PIN)
read (1Z,3E)- (1Z,3E)-cyclocosa-1,3-dien-5-yne (PIN)

P-44.4.1.10.1 (2), example right. [corrected 4 September 2024]
For cyclocosa-1,5-dien-3-yne (PIN)
read (1E,5E)- cyclocosa-1,5-dien-3-yne (PIN)

P-46.1.12, example 1 right. [corrected 9 October 2024]
For [not 3-hydroxy-1-(1- hydroxyethyl)propyl
read [not 3-hydroxy-1-(1-hydroxyethyl)propyl

P-54.2, example 2. [corrected 4 September 2024]
Replace the structure with:
   
for cyclododeca-1,3,5,7,9-pentaen-11-yne (PIN)
read (1Z,3E,5Z,7E,9Z)-cyclododeca-1,3,5,7,9-pentaen-11-yne (PIN)
for 1,2-didehydro[12]annulene
read 1,2-didehydro[12]annulene (numbering shown)

P-64.2.2.3, example 8. [corrected 4 September 2024]
For 1,3,6,8(2,5)-tetrafuranacyclododecaphan-11-en-2-one (PIN)
read (11Z)-1,4,7,10(2,5)-tetrafuranacyclododecaphan-11-en-2-one (PIN)

P-65.3.3.2.2.1 (2), lines 2/3. [corrected 28 May 2024]
For ...representing the ‘hydroxylic’ are exactly...
read ...representing the ‘hydroxylic’ component are exactly...

P-65.6.3.3.2.2.1, example 1. [corrected 28 May 2024]
For (2) 3,3′-oxydi(methyl benzoate)
read (2) 3,3′-oxybis(methyl benzoate)

Page 809, P-65.6.3.3.2.2.1, example 3. [corrected 9 October 2024]
For (2) butanedioylbis(oxy-2,1-phenylene) di(methyl butanedioate)
read (2) butanedioylbis(oxy-2,1-phenylene) bis(methyl butanedioate)

P-65.6.3.3.4.1, example. [corrected 28 May 2024]
For ethane-1,2-diyl di(methyl butanedioate)
read ethane-1,2-diyl bis(methyl butanedioate)

P-69.2.4, example 2. [corrected 9 October 2024]
For [(2,3,5,6-η) -bicyclo[2.2.1]hepta-2,5-diene]tricarbonyliron
read [(2,3,5,6-η)-bicyclo[2.2.1]hepta-2,5-diene]tricarbonyliron

Page 1105, P-73.6, example 2. [corrected 9 October 2024]
For triaz-2-en-1-ium-1- yl (preselected prefix)
read triaz-2-en-1-ium-1-yl (preselected prefix)

P-93.5.5.1, example 2. [corrected 28 May 2024]
For (14M)-15-bromo-2,13-dioxa-1(1,4)-benzenacyclotridecaphane-12-carboxylic acid (PIN)
read (14M)-15-bromo-2,13-dioxa-1(1,4)-benzenacyclotridecaphane-12-carboxylic acid

add (1M)-17-bromo-2,13-dioxabicyclo[12.2.2]octadeca-1(16),14,17-triene-15-carboxylic acid (PIN)

P-93.5.5.3, lines 3/4. [corrected 4 September 2024]
For ...present, all descriptors are must be cited (see P-91.2.2).
read ...present, all descriptors of double bonds in rings of more than seven nodes are cited (see P-91.2.2)

P-93.5.5.3, example 2. [corrected 4 September 2024]
For (2E)-1(2,6)-pyridina-7(1,3)-benzenacyclododecaphan-2-ene (PIN)
read (2E)-11,14,15,16-tetrahydro-1(2,6)-pyridina-7(1,3)-benzenacyclododecaphan-2-ene (PIN)

Appendix 2, heptanylidene*. [corrected 9 October 2024]
For CH3-[CH2]5 -CH=
read CH3-[CH2]5-CH=

Appendix 2. [corrected 9 October 2024]
For 7- isoquinolyl
read 7-isoquinolyl

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